EP0518113A1 - Pancement de nitroglycerine et son procédé de préparation - Google Patents
Pancement de nitroglycerine et son procédé de préparation Download PDFInfo
- Publication number
- EP0518113A1 EP0518113A1 EP92108798A EP92108798A EP0518113A1 EP 0518113 A1 EP0518113 A1 EP 0518113A1 EP 92108798 A EP92108798 A EP 92108798A EP 92108798 A EP92108798 A EP 92108798A EP 0518113 A1 EP0518113 A1 EP 0518113A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- nitroglycerin
- weight
- vinyl acetate
- acrylate
- plaster
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000011505 plaster Substances 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title abstract description 4
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 claims abstract description 43
- 239000000006 Nitroglycerin Substances 0.000 claims abstract description 43
- 229960003711 glyceryl trinitrate Drugs 0.000 claims abstract description 43
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 229920001577 copolymer Polymers 0.000 claims abstract description 20
- 239000000853 adhesive Substances 0.000 claims abstract description 17
- 230000001070 adhesive effect Effects 0.000 claims abstract description 16
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 239000000178 monomer Substances 0.000 claims abstract description 7
- 230000001681 protective effect Effects 0.000 claims abstract description 6
- 239000004971 Cross linker Substances 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 239000007933 dermal patch Substances 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- 239000003431 cross linking reagent Substances 0.000 claims description 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 7
- 238000004132 cross linking Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical group OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 238000010526 radical polymerization reaction Methods 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- 239000010936 titanium Substances 0.000 claims description 5
- RYSXWUYLAWPLES-MTOQALJVSA-N (Z)-4-hydroxypent-3-en-2-one titanium Chemical group [Ti].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RYSXWUYLAWPLES-MTOQALJVSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000011877 solvent mixture Substances 0.000 claims description 4
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- 206010040880 Skin irritation Diseases 0.000 abstract description 2
- 230000036556 skin irritation Effects 0.000 abstract description 2
- 231100000475 skin irritation Toxicity 0.000 abstract description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- 230000002500 effect on skin Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229920006267 polyester film Polymers 0.000 description 6
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 3
- 239000003655 absorption accelerator Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000003791 organic solvent mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002998 adhesive polymer Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
- A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
- A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
- A61K9/7061—Polyacrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Definitions
- the present invention relates to a skin patch for the transdermal administration of nitroglycerin, consisting of a carrier film and an adhesive composition containing nitroglycerin based on a crosslinked acrylate copolymer.
- the patch also has a protective film which is applied to the patch prior to use, e.g. removed before peeling it off the skin.
- Skin patches for the transdermal administration of nitroglycerin are well known.
- DE 2135533 and DE 3315272 describe plasters which have a multilayer structure and control the release of active substance. Nitroglycerin is released by various mechanisms, be it from a single-layer reservoir through a control membrane (DE 2135533) or be it through the special design of the multi-layer reservoir (DE 3315272). Since the multilayered skin plasters are particularly expensive to manufacture, plasters have recently been developed which are composed of a single layer in addition to the carrier film.
- the plasters Depending on the materials used and the degree of crosslinking, the plasters have different absorption capacities and dispensability for nitroglycerin and are characterized by different adhesiveness to the skin. Different skin tolerances also play an important role. Some of the plasters also contain substances to increase transepidermal mass transport (so-called absorption accelerators).
- the object of the present invention is to provide a skin patch for the transdermal administration of nitroglycerin, which is characterized by the use of a pressure sensitive adhesive which not only has the highest possible absorption capacity, but also has a high dispensing capacity for nitroglycerin, so that the release area for the required amount of release per day of the patch can be kept small, thereby minimizing the cost of the patch.
- a special adhesive is intended to simplify the manufacturing process, reduce its costs and save on the addition of absorption accelerators. This simplification of the pharmaceutical formulation also reduces the risk of skin irritation and / or an uncontrollable change in the nitroglycerin concentration in the PSA, which can be associated with the penetration of absorption accelerators from the adhesive into the skin.
- the skin patch according to the invention for the transdermal administration of nitroglycerin consisting of a carrier film, a nitroglycerin-containing adhesive based on a crosslinked acrylate-vinyl acetate copolymer and a customary removable protective film is characterized in that the adhesive composition containing the nitroglycerin is obtained in that in a first stage a mixture of 21 to 40% by weight of vinyl acetate, 55 to 70% by weight of an acrylic acid C2 Acryl-alkyl ester and 3 to 10 % By weight of an acrylic acid-C2 ⁇ 4-hydroxyacrylic ester, with 100% by weight of monomers in a mixture, is subjected to a radical polymerization in an organic solvent, then in a second stage a customary crosslinking agent in an organic solvent and the nitroglycerin in the the amount necessary for the intended application of the patch, optionally mixed in an organic solvent, and finally, in a third stage, the mixture obtained or the particular acrylate-vinyl acetate copo
- the monomer mixture preferably contains 2-ethylhexyl acrylate and hydroxyethyl acrylate.
- the subsequent crosslinking of the particular acrylate-vinyl acetate copolymer with a titanium acid ester consisting of polybutyl titanate and / or titanium acetylacetonate is preferred, in particular in an amount of 0.3 to 3% by weight thereof, the percentages by weight based on the weight of the copolymer.
- the process for the preparation of the patch according to the invention is characterized in that a nitroglycerin in the for the intended application of the Plaster necessary amount and a conventional crosslinker or a conventional crosslinker mixture containing solution by radical polymerization of a monomer mixture consisting of 21 to 40 wt .-% vinyl acetate, 55 to 70 wt .-% of an acrylic acid C2 ⁇ 8-alkyl ester and 3 to 10 wt .-% of an acrylic acid-C2 ⁇ 4-hydroxyalkyl ester copolymer is applied to the protective film of the patch in the desired layer thickness and the solvent or solvent mixture is removed with heating and so the additional crosslinking of the special acrylate-vinyl acetate copolymer is carried out.
- the process is preferably characterized in that the acrylate-vinyl acetate copolymer, nitroglycerin and crosslinker are dissolved in a solvent which contains 20 to 40% by weight of ethanol or an ethanol-methanol mixture, with a solids content consisting of 40 to 60% by weight of the mixture of the special acrylate-vinyl acetate copolymer, crosslinking agent and the nitroglycerin.
- the acrylate-vinyl acetate copolymer is produced as follows: Of the total amount of 112 g vinyl acetate, 270 g 2-ethylhexyl acrylate, 20 g hydroxyethyl acrylate, 1.4 g azodiisobutyronitrile and 407 g ethyl acetate, 112 g vinyl acetate, 39 g 2-ethylhexyl acrylate, 3 g hydroxyethyl acrylate and 0.5 g azodiisobutyronitrile are added Ethyl acetate added and heated to reflux. The remaining portion of the ingredients is added over a period of 4 hours under constant reflux.
- the resulting adhesive polymer solution has a viscosity of 5300 mPa.s at 25 o C, measured with a Brookfield viscometer, a solids content of 47.9% and the relative viscosity is 3.1.
- the above-mentioned 20% (w / w) nitroglycerin-containing adhesive solution is applied to a 100 ⁇ m thick siliconized polyester film, so that a film with a basis weight of 92 g / m 2 results after removal of the solvent.
- This film is covered with a 19 ⁇ m thick polyester film and punched into plasters with a contact area of 16 qcm (Fig. 1 and 2).
- a skin patch with a weight of 420 mg contains 55 mg nitroglycerin.
- a plaster with a punched-out area of 3.14 qcm is used in a modified Franz diffusion cell (see Chien, Yie W., Drugs of Today Vol. 23, No. 11 (1987) 625-646). attached to a skin preparation of hairless mice.
- the cell is filled with 18.00 ml of isotonic phosphate buffer solution (32 ⁇ 0.5 o C) without air bubbles and thermostatted to 32 ⁇ 0.5 o C.
- the release medium is replaced by fresh solution thermostated to 32 ⁇ 0.5 o C.
- the release profile for a 16 qcm plaster measured according to this method is shown in Fig. 3.
- the above-mentioned 20% (w / w) nitroglycerin-containing adhesive solution is additionally 0.8% (w / w) titanium acetylacetonate (manufacturer: Dynamit Nobel Nederland BV, 75% (w / w) solution in isopropanol), based on a 40% (w / w) solids content of the polyacrylate adhesive solution plus nitroglycerin, added and the mixture homogenized.
- This solution is applied to a 100 ⁇ m thick siliconized polyester film, so that a film with a basis weight of 93 g / m 2 results after removal of the solvent.
- This film is covered with a 19 ⁇ m thick polyester film and punched into plasters with a contact area of 16 qcm (Fig. 1 and 2).
- a skin patch with a weight of 420 mg contains 55 mg nitroglycerin.
- the drug release in vitro was carried out according to the method in Example 1.
- the corresponding release profile is also shown graphically in Fig. 3.
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Dermatology (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4118891 | 1991-06-10 | ||
| DE4118891 | 1991-06-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0518113A1 true EP0518113A1 (fr) | 1992-12-16 |
Family
ID=6433497
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP92911100A Expired - Lifetime EP0588839B1 (fr) | 1991-06-10 | 1992-05-25 | Emplatre a la nitroglycerine et son procede de fabrication |
| EP92108798A Pending EP0518113A1 (fr) | 1991-06-10 | 1992-05-25 | Pancement de nitroglycerine et son procédé de préparation |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP92911100A Expired - Lifetime EP0588839B1 (fr) | 1991-06-10 | 1992-05-25 | Emplatre a la nitroglycerine et son procede de fabrication |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5498418A (fr) |
| EP (2) | EP0588839B1 (fr) |
| JP (1) | JP2579729B2 (fr) |
| KR (1) | KR0165875B1 (fr) |
| CN (1) | CN1053591C (fr) |
| AT (1) | ATE126434T1 (fr) |
| CA (1) | CA2109956C (fr) |
| DE (1) | DE59203307D1 (fr) |
| DK (1) | DK0588839T3 (fr) |
| ES (1) | ES2077419T3 (fr) |
| FI (1) | FI101854B (fr) |
| GE (1) | GEP19991583B (fr) |
| GR (1) | GR3017689T3 (fr) |
| HU (1) | HU210334B (fr) |
| IE (1) | IE67792B1 (fr) |
| NO (2) | NO934518D0 (fr) |
| UA (1) | UA29400C2 (fr) |
| WO (1) | WO1992022292A1 (fr) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0622075A1 (fr) * | 1993-04-27 | 1994-11-02 | Hercon Laboratories Corporation | Administration transdermique de médicaments actifs |
| WO1998025591A1 (fr) * | 1996-12-10 | 1998-06-18 | Rotta Research B.V. | Systeme d'administration de medicaments transdermiques pour le traitement des maladies du coeur |
| EP0856311A1 (fr) * | 1996-12-10 | 1998-08-05 | Rotta Research B.V. | Système transdermique pour l'administration d'un médicament pour le traitement des maladies du coeur |
| WO1999055327A1 (fr) * | 1998-04-28 | 1999-11-04 | Lts Lohmann Therapie-Systeme Ag | Composition contenant du polyacrylate, du polyterpene, de la nitroglycerine et eventuellement du polyvinyle acetate |
| WO2007038323A1 (fr) * | 2005-09-23 | 2007-04-05 | National Starch And Chemical Investment Holding Corporation | Adhesifs acryliques a base de polymeres |
| WO2007038322A1 (fr) * | 2005-09-23 | 2007-04-05 | National Starch And Chemical Investment Holding Corporation | Adhesifs acryliques a base de polymeres |
| DE202016007127U1 (de) | 2016-11-22 | 2016-12-19 | Ludwig Volker | Falzhilfe |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4406332C1 (de) * | 1994-02-28 | 1995-06-22 | Sanol Arznei Schwarz Gmbh | Pharmazeutische Verwendung von Nitroglycerin zur Verhinderung unerwünschter Wehentätigkeit bei Säugern in einer transdermalen Applikationsform |
| US20020048596A1 (en) * | 1994-12-30 | 2002-04-25 | Gregor Cevc | Preparation for the transport of an active substance across barriers |
| CN1070367C (zh) * | 1997-08-07 | 2001-09-05 | 德阳华康药业有限公司 | 注射贴及其制备方法 |
| DE19830648A1 (de) * | 1998-07-09 | 2000-01-13 | Lohmann Therapie Syst Lts | Glyceroltrinitrathaltige Zusammensetzung, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19831418C2 (de) * | 1998-07-14 | 2000-07-06 | Lohmann Therapie Syst Lts | Verfahren und Vorrichtung zum Herstellen flächenhafter Produkte aus Laminat, deren Übertragung auf eine Abdeckfolie und Endkonfektionierung |
| AU770803B2 (en) | 1998-12-23 | 2004-03-04 | Idea Ag | Improved formulation for topical non-invasive application in vivo |
| ATE216875T1 (de) | 1999-01-27 | 2002-05-15 | Idea Ag | Nichtinvasive impfung durch die haut |
| PT1031347E (pt) | 1999-01-27 | 2002-09-30 | Idea Ag | Transporte/imunizacao transnasal com veiculos muitissimo adaptaveis |
| AU5409699A (en) | 1999-07-05 | 2001-01-22 | Idea Ag | A method for the improvement of transport across adaptable semi-permeable barriers |
| JP5021124B2 (ja) * | 2001-08-29 | 2012-09-05 | 日東電工株式会社 | 医療用粘着組成物、それを用いた医療用粘着テープおよび経皮吸収用テープ製剤 |
| DK1293198T3 (da) * | 2001-09-14 | 2005-06-06 | Sanol Arznei Schwarz Gmbh | Anordning til transdermal indgivelse til behandling af urinkanallidelser |
| CN1655772B (zh) * | 2002-05-28 | 2010-05-26 | 拉伯泰克技术研发有限公司 | 含有芬太尼的贴剂 |
| US7473432B2 (en) * | 2002-10-11 | 2009-01-06 | Idea Ag | NSAID formulations, based on highly adaptable aggregates, for improved transport through barriers and topical drug delivery |
| KR100563194B1 (ko) * | 2003-11-14 | 2006-03-21 | (주) 에프디엘 | 펜타닐을 유효성분으로 함유하는 경피투여제제 |
| JP2008519784A (ja) * | 2004-11-12 | 2008-06-12 | イデア アクチェンゲゼルシャフト | 皮膚状態の治療における拡張表面凝集体 |
| BR112017003248B1 (pt) * | 2014-08-25 | 2022-10-11 | Henkel IP & Holding GmbH | Composição compreendendo copolímero acrílico |
| CN105362254B (zh) * | 2015-12-09 | 2017-03-15 | 北京邦尼康达医药科技有限公司 | 一种硝酸甘油贴膜及其制备方法 |
| CN113125596B (zh) * | 2021-04-07 | 2023-01-13 | 马应龙药业集团股份有限公司 | 一种高效液相色谱法测定硝酸甘油软膏中有关物质的方法 |
Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2135533A1 (de) | 1969-04-01 | 1973-02-01 | Alza Corp | Medizinischer verband |
| GB2086224A (en) | 1980-10-30 | 1982-05-12 | Nitto Electric Ind Co | Antiphlogistic/analgesic adhesive pharmaceutical preparation |
| DE3200369A1 (de) | 1981-01-08 | 1982-08-05 | Nitto Electric Industrial Co., Ltd., Ibaraki, Osaka | Pharmazeutisches praeparat |
| GB2095108A (en) | 1981-03-13 | 1982-09-29 | Nitto Electric Ind Co | Process for obtaining composite pharmaceutical preparation containing a percutaneous medicine |
| EP0062682A1 (fr) | 1980-10-20 | 1982-10-20 | Nichiban Co. Ltd. | Preparation adhesive pour les maladies du coeur et son procede de preparation |
| DE3231400A1 (de) | 1981-08-27 | 1983-03-10 | Nitto Electric Ind Co | Selbsthaftendes medizinisches verbundpraeparat |
| DE3315272A1 (de) | 1983-04-27 | 1984-10-31 | Lohmann Gmbh & Co Kg, 5450 Neuwied | Pharmazeutisches produkt |
| EP0190262A1 (fr) | 1984-07-24 | 1986-08-13 | Key Pharma | Couche adhesive de dosage transdermal. |
| US4608249A (en) | 1982-11-02 | 1986-08-26 | Nitto Electric Industrial Co., Ltd. | Hydrophilic therapeutic material |
| WO1986006281A1 (fr) * | 1985-04-19 | 1986-11-06 | Riker Laboratories, Inc. | Systeme d'administration transcutanee de nitroglycerine |
| EP0272562A2 (fr) | 1986-12-22 | 1988-06-29 | LTS Lohmann Therapie-Systeme GmbH & Co. KG | Masse polymère adhésive basique laissant passer l'agent actif, procédé de préparation et utilisation |
| EP0285550A2 (fr) | 1987-03-31 | 1988-10-05 | Sekisui Kagaku Kogyo Kabushiki Kaisha | Préparation pharmaceutique de nitroglycérine pour l'administration percutanée |
| EP0427877A1 (fr) * | 1988-05-11 | 1991-05-22 | Nitto Denko Corporation | Préparation de clonidine sous forme de bande adhÀ©sive |
| EP0435199A2 (fr) * | 1989-12-28 | 1991-07-03 | Nitto Denko Corporation | Gel acrylique et sa préparation |
| EP0450986A2 (fr) * | 1990-04-06 | 1991-10-09 | Sekisui Kagaku Kogyo Kabushiki Kaisha | Préparation pharmaceutique pour l'administration percutanée de nitroglycérine |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62292877A (ja) * | 1986-06-13 | 1987-12-19 | Nippon Shokubai Kagaku Kogyo Co Ltd | 接着剤用組成物 |
| US4994267A (en) * | 1988-03-04 | 1991-02-19 | Noven Pharmaceuticals, Inc. | Transdermal acrylic multipolymer drug delivery system |
| US4814168A (en) * | 1988-03-04 | 1989-03-21 | Noven Pharmaceuticals, Inc. | Transdermal multipolymer drug delivery system |
| JP2970772B2 (ja) * | 1989-12-28 | 1999-11-02 | 日東電工株式会社 | 経皮吸収ゲル製剤 |
| JP2882843B2 (ja) * | 1990-03-28 | 1999-04-12 | 日本化薬株式会社 | 門脈圧亢進症改善剤 |
-
1992
- 1992-05-25 WO PCT/EP1992/001169 patent/WO1992022292A1/fr not_active Ceased
- 1992-05-25 HU HU9303532A patent/HU210334B/hu unknown
- 1992-05-25 JP JP4510428A patent/JP2579729B2/ja not_active Expired - Lifetime
- 1992-05-25 KR KR1019930703733A patent/KR0165875B1/ko not_active Expired - Lifetime
- 1992-05-25 UA UA93004272A patent/UA29400C2/uk unknown
- 1992-05-25 ES ES92911100T patent/ES2077419T3/es not_active Expired - Lifetime
- 1992-05-25 EP EP92911100A patent/EP0588839B1/fr not_active Expired - Lifetime
- 1992-05-25 US US08/142,316 patent/US5498418A/en not_active Expired - Lifetime
- 1992-05-25 DE DE59203307T patent/DE59203307D1/de not_active Expired - Lifetime
- 1992-05-25 AT AT92911100T patent/ATE126434T1/de active
- 1992-05-25 CA CA002109956A patent/CA2109956C/fr not_active Expired - Lifetime
- 1992-05-25 DK DK92911100.3T patent/DK0588839T3/da active
- 1992-05-25 GE GEAP19922563A patent/GEP19991583B/en unknown
- 1992-05-25 EP EP92108798A patent/EP0518113A1/fr active Pending
- 1992-06-09 CN CN92105694A patent/CN1053591C/zh not_active Expired - Lifetime
- 1992-07-01 IE IE921863A patent/IE67792B1/en not_active IP Right Cessation
-
1993
- 1993-12-09 NO NO934518D patent/NO934518D0/no unknown
- 1993-12-09 FI FI935522A patent/FI101854B/fi not_active IP Right Cessation
- 1993-12-09 NO NO934518A patent/NO305384B1/no not_active IP Right Cessation
-
1995
- 1995-10-11 GR GR950402794T patent/GR3017689T3/el unknown
Patent Citations (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2135533A1 (de) | 1969-04-01 | 1973-02-01 | Alza Corp | Medizinischer verband |
| EP0062682A1 (fr) | 1980-10-20 | 1982-10-20 | Nichiban Co. Ltd. | Preparation adhesive pour les maladies du coeur et son procede de preparation |
| GB2086224A (en) | 1980-10-30 | 1982-05-12 | Nitto Electric Ind Co | Antiphlogistic/analgesic adhesive pharmaceutical preparation |
| DE3200369A1 (de) | 1981-01-08 | 1982-08-05 | Nitto Electric Industrial Co., Ltd., Ibaraki, Osaka | Pharmazeutisches praeparat |
| GB2095108A (en) | 1981-03-13 | 1982-09-29 | Nitto Electric Ind Co | Process for obtaining composite pharmaceutical preparation containing a percutaneous medicine |
| DE3231400A1 (de) | 1981-08-27 | 1983-03-10 | Nitto Electric Ind Co | Selbsthaftendes medizinisches verbundpraeparat |
| US4608249A (en) | 1982-11-02 | 1986-08-26 | Nitto Electric Industrial Co., Ltd. | Hydrophilic therapeutic material |
| DE3315272A1 (de) | 1983-04-27 | 1984-10-31 | Lohmann Gmbh & Co Kg, 5450 Neuwied | Pharmazeutisches produkt |
| EP0190262A1 (fr) | 1984-07-24 | 1986-08-13 | Key Pharma | Couche adhesive de dosage transdermal. |
| WO1986006281A1 (fr) * | 1985-04-19 | 1986-11-06 | Riker Laboratories, Inc. | Systeme d'administration transcutanee de nitroglycerine |
| EP0219539A1 (fr) | 1985-04-19 | 1987-04-29 | Riker Laboratories Inc | Systeme d'administration transcutanee de nitroglycerine. |
| EP0272562A2 (fr) | 1986-12-22 | 1988-06-29 | LTS Lohmann Therapie-Systeme GmbH & Co. KG | Masse polymère adhésive basique laissant passer l'agent actif, procédé de préparation et utilisation |
| EP0285550A2 (fr) | 1987-03-31 | 1988-10-05 | Sekisui Kagaku Kogyo Kabushiki Kaisha | Préparation pharmaceutique de nitroglycérine pour l'administration percutanée |
| EP0427877A1 (fr) * | 1988-05-11 | 1991-05-22 | Nitto Denko Corporation | Préparation de clonidine sous forme de bande adhÀ©sive |
| EP0435199A2 (fr) * | 1989-12-28 | 1991-07-03 | Nitto Denko Corporation | Gel acrylique et sa préparation |
| EP0450986A2 (fr) * | 1990-04-06 | 1991-10-09 | Sekisui Kagaku Kogyo Kabushiki Kaisha | Préparation pharmaceutique pour l'administration percutanée de nitroglycérine |
Non-Patent Citations (4)
| Title |
|---|
| CHEMICAL ABSTRACTS, Band 97, Nr. 12, September 1982, Seite 403, Zusammenfassung Nr. 98386f, Columbus, Ohio, US; & JP-A-82 107 155 (NITTO ELECTRIC INDUSTRIAL CO., LTD) 03-07-1982 * |
| CHIEN, YIE W., DRUGS OF TODAY, vol. 23, no. 11, 1987, pages 625 - 646 |
| DERWENT FILE SUPPLIER & BASE WPIL, AN=88-033094 [05], Derwent Publications Ltd, London, GB; & JP-A-62 292 877 (NIPPON SHOKUBAI KAGAKU) 19-12-1987 * |
| LIT., PHARM.BIOL., vol. 4, 1981, pages 32 |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0622075A1 (fr) * | 1993-04-27 | 1994-11-02 | Hercon Laboratories Corporation | Administration transdermique de médicaments actifs |
| US5762952A (en) * | 1993-04-27 | 1998-06-09 | Hercon Laboratories Corporation | Transdermal delivery of active drugs |
| WO1998025591A1 (fr) * | 1996-12-10 | 1998-06-18 | Rotta Research B.V. | Systeme d'administration de medicaments transdermiques pour le traitement des maladies du coeur |
| EP0856311A1 (fr) * | 1996-12-10 | 1998-08-05 | Rotta Research B.V. | Système transdermique pour l'administration d'un médicament pour le traitement des maladies du coeur |
| WO1999055327A1 (fr) * | 1998-04-28 | 1999-11-04 | Lts Lohmann Therapie-Systeme Ag | Composition contenant du polyacrylate, du polyterpene, de la nitroglycerine et eventuellement du polyvinyle acetate |
| WO2007038323A1 (fr) * | 2005-09-23 | 2007-04-05 | National Starch And Chemical Investment Holding Corporation | Adhesifs acryliques a base de polymeres |
| WO2007038322A1 (fr) * | 2005-09-23 | 2007-04-05 | National Starch And Chemical Investment Holding Corporation | Adhesifs acryliques a base de polymeres |
| US8153742B2 (en) | 2005-09-23 | 2012-04-10 | Henkel Ag & Co. Kgaa | Acrylic polymer-based adhesives |
| US8263680B2 (en) | 2005-09-23 | 2012-09-11 | Henkel Ag & Co. Kgaa | Acrylic polymer-based adhesives |
| DE202016007127U1 (de) | 2016-11-22 | 2016-12-19 | Ludwig Volker | Falzhilfe |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1053591C (zh) | 2000-06-21 |
| DE59203307D1 (de) | 1995-09-21 |
| NO934518L (no) | 1993-12-09 |
| FI101854B1 (fi) | 1998-09-15 |
| HU9303532D0 (en) | 1994-04-28 |
| US5498418A (en) | 1996-03-12 |
| EP0588839A1 (fr) | 1994-03-30 |
| CA2109956C (fr) | 1998-05-05 |
| IE67792B1 (en) | 1996-04-17 |
| FI935522A0 (fi) | 1993-12-09 |
| NO305384B1 (no) | 1999-05-25 |
| WO1992022292A1 (fr) | 1992-12-23 |
| FI101854B (fi) | 1998-09-15 |
| JP2579729B2 (ja) | 1997-02-12 |
| CA2109956A1 (fr) | 1992-12-23 |
| EP0588839B1 (fr) | 1995-08-16 |
| GEP19991583B (en) | 1999-04-29 |
| HUT65979A (en) | 1994-08-29 |
| FI935522A7 (fi) | 1993-12-09 |
| UA29400C2 (uk) | 2000-11-15 |
| GR3017689T3 (en) | 1996-01-31 |
| JPH06506944A (ja) | 1994-08-04 |
| CN1072093A (zh) | 1993-05-19 |
| ES2077419T3 (es) | 1995-11-16 |
| DK0588839T3 (da) | 1995-12-27 |
| KR0165875B1 (ko) | 1999-01-15 |
| NO934518D0 (no) | 1993-12-09 |
| ATE126434T1 (de) | 1995-09-15 |
| IE921863A1 (en) | 1992-12-16 |
| HU210334B (en) | 1995-03-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0588839B1 (fr) | Emplatre a la nitroglycerine et son procede de fabrication | |
| EP1492517B1 (fr) | Systeme therapeutique transdermique (stt) pour administrer de la rotigotine | |
| EP0186019B1 (fr) | Pansement médicamenteux | |
| EP0617972B1 (fr) | Système thérapeutique dermique à base d'un mélange de polyméthacrylates fusibles | |
| DE3685545T2 (de) | System zur transdermalen abgabe von nitroglycerin. | |
| EP1033978B1 (fr) | Systeme therapeutique transdermique contenant un agoniste d2 servant a traiter le syndrome parkinsonien, et son procede de production | |
| DE69822327T2 (de) | Transdermales arzneistoff-abgabesystem für ein entzündungshemmendes analgetisches mittel enthaltend diclofenac diethylammonium salz, und verfahren zu dessen herstellung | |
| DE69020875T2 (de) | Oestrogenhaltiges Gelpräparat. | |
| DE69205010T2 (de) | Transdermales estradiol als therapeutisches system. | |
| DE69218932T2 (de) | Transdermale therapeutische Formulierung | |
| DE69108683T2 (de) | Zubereitung zur transdermalen Verabreichung von Arzneimitteln. | |
| DE68917292T2 (de) | Transdermales estradiol als therapeutisches sytem. | |
| EP0439180A2 (fr) | Système thérapeutique transdermique pour l'agent actif tulobuterol | |
| EP0305726B1 (fr) | Système transdermique thérapeutique | |
| WO2002045699A2 (fr) | Systeme therapeutique transdermique contenant l'agent actif oxybutynine | |
| DE3587048T2 (de) | Pharmazeutische praeparate. | |
| EP1178782A2 (fr) | Systeme therapeutique transdermique (stt) contenant de la tolterodine | |
| DE19629468A1 (de) | Transdermale therapeutische Systeme | |
| EP0709088B1 (fr) | Système d'administration transdermique de naloxone | |
| EP0966273B1 (fr) | Systeme a emplatre transdermique ou topique avec matrice au polyacrylate a proprietes physiques ameliorees | |
| DE3873581T2 (de) | Nitroglycerinarzneimittelpraeparat fuer perkutane absorption. | |
| DE4333595A1 (de) | Transdermales therapeutisches System zur Applikation von Arzneimitteln auf die Haut | |
| DE3911699C2 (de) | Pharmazeutische Zubereitung mit einem perkutan absorbierbaren Arzneimittel | |
| EP1063983A1 (fr) | Systeme therapeutique transdermique (tts) contenant de l'oxybutynine | |
| EP0781134A1 (fr) | Emplatre a la scopolamine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): PT |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: PROCEEDINGS CLOSED FOLLOWING CONSOLIDATION WITH EP92911100.3 |
|
| 17P | Request for examination filed |
Effective date: 19921223 |
|
| XX | Miscellaneous (additional remarks) |
Free format text: VERFAHREN ABGESCHLOSSEN INFOLGE VERBINDUNG MIT 92911100.3/0588839 (EUROPAEISCHE ANMELDENUMMER/VEROEFFENTLICHUNGSNUMMER) DURCH ENTSCHEIDUNG VOM 10.11.94. |